We did some searching and found that despite some views that the holiday is foreign to Judaism and should be avoided, there are a growing number of opinions, even in the Orthodox world, that not only should the holiday be observed, but that it should be embraced.
As Rabbi Benjamin Blech, professsor of Talmud at Yeshiva University, has written about Valentine's Day on the aish.com website,
As Jews, we may not be sure whether it's proper for us to join the party. After all, for the longest time the full name of this holiday was “St. Valentine's Day” because of its legendary link with the apocryphal story of one of the earliest Christian saints. Yet academics aren't the only ones who have recognized the dubious historical basis of this connection. Vatican II, the landmark set of reforms adopted by the Catholic Church in 1969, removed Valentine's Day from the Catholic church's calendar, asserting that "though the memorial of St. Valentine is ancient… apart from his name nothing is known… except that he was buried on the Via Flaminia on 14 February."
What's left for this day, as proponents of its universal celebration declare, is something that people of all faiths may in good conscience observe: A day in which to acknowledge the power of love to make us fully human.
When I am asked as a rabbi if I think it's a good idea for Jews to celebrate Valentine's Day, my standard answer is, "Yes, we should celebrate love… every day of the year."This year, to embrace Valentine's Day, we bring you A Jewish Grandparents' Guide to Romance, a video from The Forward.
A SPECIAL NOTE FOR NEW EMAIL SUBSCRIBERS: THE VIDEO MAY NOT BE VIEWABLE DIRECTLY FROM THE EMAIL THAT YOU GET EACH DAY ON SOME COMPUTERS AND TABLETS. YOU MUST CLICK ON THE TITLE AT THE TOP OF THE EMAIL TO REACH THE JEWISH HUMOR CENTRAL WEBSITE, FROM WHICH YOU CLICK ON THE PLAY BUTTON IN THE VIDEO IMAGE TO START THE VIDEO.